tributyl-amine; tris-(o-tolyl)phosphine; palladium dichloride in N,N-dimethyl-formamide T=90°C; 15 h; Inert atmosphere; regioselective reaction;

1: 91 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 2: 90 percent / methyl iodide / 96 h / 110 °C View Scheme

1: 91 percent / copper iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine / 3 h / 30 °C 2: 90 percent / methyl iodide / 96 h / 110 °C 3: 87 percent / potassium hydroxide / methanol; CH2Cl2 / 2 h View Scheme

1: Et3N / PdCl2(PPh3)2, CuI 2: 96 percent / MeI / 120 °C 3: 88 percent / Et3N / PdCl2(PPh3)2, CuI 4: MeI / 120 °C 5: Et3N / PdCl2(PPh3)2, CuI 6: MeI / 120 °C 7: K2CO3 / methanol 8: Et3N / Pd(dba)2, PPh3, CuI View Scheme